Summary of Proposed Work: Three research areas will be pursued: (1) the preparation of unsaturated gamma-lactones for study of their carcinogenic and biological activity, (2) extension of lanthanide NMR chemical shift reagents to more complex lipid derivatives and model compounds, such as peroxides, disulfides, amines and hydrazines and (3) the preparation of additional diepoxides and triepoxides and study of their hydrolysis to tetrols and hexaols, respectively. Unsaturated lactones will be examined for their effect on damage and repair of DNA in Salmonella mutants.